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Domino Methylenation/Hydrogenation of Aldehydes and Ketones by Combining Matsubara's Reagent and Wilkinson's Catalyst
Author(s) -
Maazaoui Radhouan,
PinNó María,
Gervais Kevin,
Abderrahim Raoudha,
Ferreira Franck,
PerezLuna Alejandro,
Chemla Fabrice,
Jackowski Olivier
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601137
Subject(s) - chemoselectivity , domino , reagent , chemistry , catalysis , compatibility (geochemistry) , cascade reaction , cascade , organic chemistry , combinatorial chemistry , materials science , chromatography , composite material
The methylenation/hydrogenation cascade reaction of aldehydes or ketones through a domino process involving two ensuing steps in a single pot is realized. The compatibility of Matsubara's reagent and Wilkinson's complex give a combination that allows, under dihydrogen, the transformation of a carbonyl function into a methyl group. This new method is suitable to introduce an ethyl motif from aromatic and aliphatic aldehydes with total chemoselectivity and total retention of α‐stereochemical purity. The developed procedure is also extended to the introduction of methyl groups from ketones.